N-(4-chloro-2-pyridin-3-yl-pyrimidin-5-yl)-2,2,2-trifluoroacetamide | 1562399-19-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: N-(4-chloro-2-pyridin-3-yl-pyrimidin-5-yl)-2,2,2-trifluoroacetamide
• 英文别名: N-(4-chloro-2-pyridin-3-ylpyrimidin-5-yl)-2,2,2-trifluoroacetamide
• CAS: 1562399-19-2
• 化学式: C₁₁H₆ClF₃N₄O
• 分子量: 302.643
• InChiKey: IOHAEHVUWBMJHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  67.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-(5-fluoro-2-methylphenyl)-6-methyl-4-trifluoromethylhept-1-yn-4-ol 、 N-(4-chloro-2-pyridin-3-yl-pyrimidin-5-yl)-2,2,2-trifluoroacetamide 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 作用下， 以 乙腈 为溶剂， 反应 2.08h， 以57%的产率得到1,1,1-trifluoro-4-(5-fluoro-2-methylphenyl)-4-methyl-2-(2-pyridin-3-yl-5H-pyrrolo[3,2-d]pyrimidin-6-ylmethyl)pentan-2-ol
  参考文献：
  名称：

  Identification of Highly Efficacious Glucocorticoid Receptor Agonists with a Potential for Reduced Clinical Bone Side Effects

  摘要：

  Synthesis and structure-activity relationship (SAR) of a series of nonsteroidal glucocorticoid receptor (GR) agonists are described. These compounds contain "diazaindole" moieties and display different transcriptional regulatory profiles in vitro and are considered "dissociated" between gene transrepression and transactivation. The lead optimization effort described in this article focused in particular on limiting the transactivation of genes which result in bone side effects and these were assessed in vitro in MG-63 osteosarcoma cells, leading to the identification of (R)-18 and (R)-21. These compounds maintained anti-inflammatory activity in vivo in collagen induced arthritis studies in mouse but had reduced effects on bone relevant parameters compared to the widely used synthetic glucocorticoid prednisolone 2 in vivo. To our knowledge, we are the first to report on selective glucocorticoid ligands with reduced bone loss in a preclinical in vivo model.

  DOI：

  10.1021/jm4019178
• 作为产物：
  描述：

  5-nitro-2-pyridin-3-yl-3H-pyrimidin-4-one 在 盐酸 、 tin(II) chloride dihdyrate 、 溶剂黄146 、 三氯氧磷 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.5h， 生成 N-(4-chloro-2-pyridin-3-yl-pyrimidin-5-yl)-2,2,2-trifluoroacetamide
  参考文献：
  名称：

  Identification of Highly Efficacious Glucocorticoid Receptor Agonists with a Potential for Reduced Clinical Bone Side Effects

  摘要：

  Synthesis and structure-activity relationship (SAR) of a series of nonsteroidal glucocorticoid receptor (GR) agonists are described. These compounds contain "diazaindole" moieties and display different transcriptional regulatory profiles in vitro and are considered "dissociated" between gene transrepression and transactivation. The lead optimization effort described in this article focused in particular on limiting the transactivation of genes which result in bone side effects and these were assessed in vitro in MG-63 osteosarcoma cells, leading to the identification of (R)-18 and (R)-21. These compounds maintained anti-inflammatory activity in vivo in collagen induced arthritis studies in mouse but had reduced effects on bone relevant parameters compared to the widely used synthetic glucocorticoid prednisolone 2 in vivo. To our knowledge, we are the first to report on selective glucocorticoid ligands with reduced bone loss in a preclinical in vivo model.

  DOI：

  10.1021/jm4019178

文献信息

• [EN] HERBICIDALLY ACTIVE PYRIDYL-/PYRIMIDYL-PYRIMIDINE DERIVATIVES<br/>[FR] DÉRIVÉS DE PYRIDYLE-/ PYRIMIDYLE-PYRIMIDINE HERBICIDES
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2019057721A1

  公开（公告）日：2019-03-28

  The present invention relates to herbicidally active pyridyl-/pyrimidyl-pyrimidine derivatives. The invention further provides processes and intermediates used for the preparation of such derivatives. The invention further extends to herbicidal compositions comprising such derivatives, as well as to the use of such compounds and compositions in controlling undesirable plant growth: in particular the use in controlling weeds, in crops of useful plants.

  本发明涉及除草活性吡啶基/嘧啶基-嘧啶衍生物。该发明还提供了用于制备这类衍生物的工艺和中间体。该发明还涉及包含这类衍生物的除草剂组合物，以及在控制不良植物生长方面使用这些化合物和组合物，特别是在作物中控制杂草的使用。
• HERBICIDALLY ACTIVE PYRIDYL-/PYRIMIDYL-PYRIMIDINE DERIVATIVES
  申请人：Syngenta Participations AG

  公开号：EP3684183B1

  公开（公告）日：2021-11-10
• Herbicidally Active Pyridyl-/Pyrimidyl-Pyrimidine Derivatives
  申请人：Syngenta Participations AG

  公开号：US20200267980A1

  公开（公告）日：2020-08-27

  The present invention relates to herbicidally active pyridyl-/pyrimidyl-pyrimidine derivatives. The invention further provides processes and intermediates used for the preparation of such derivatives. The invention further extends to herbicidal compositions comprising such derivatives, as well as to the use of such compounds and compositions in controlling undesirable plant growth: in particular the use in controlling weeds, in crops of useful plants.